Dithiolene metal complex colorless ir absorbers

Abstract

The invention relates to the use of compounds of formulae (I) and/or (II) as colorless IR absorbers wherein M is Ni, Pd, Pt, Au, Ir, Fe, Zn, W, Cu, Mo, In, Mn, Co, Mg, V, Cr or Ti, X 1 , X 2 and X 3 are each independently of the others sulfur or oxygen, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently of the others hydrogen, NR 7 R 8 , unsubstituted or substituted C 1 -C 18 alkyl, C 1 -C 18 alkyl wherein the alkylene chain is interrupted with oxygen, unsubstituted or substituted C 1 -C 18 alkenyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl, R 7 and R 8 , each independently of the other, being unsubstituted or substituted C 1 -C 18 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl, a further IR absorber optionally being added to the compounds of formulae (I) and (II). The invention relates also to novel dithiolene compounds of formulae (I) and (II) wherein X 1 is oxygen and X 2 and X 3 are oxygen or sulfur. The invention relates furthermore to novel dithiolene compounds of formulae (I) and (II) wherein R 1 to R 6 are NR 7 R 8 .

1 . A method of causing the IR absorbance of a material by treating said material with the colorless IR absorbers of compounds of formulae I and/or II 
       
         
           
           
               
               
           
         
       
       wherein
 M is Ni, Pd, Pt, Au, Ir, Fe, Zn, W, Cu, Mo, In, Mn, Co, Mg, V, Cr or Ti, 
 X 1 , X 2  and X 3  are each independently of the others sulfur or oxygen, 
 R 1 , R 2 , R 3 , R 4 , R 5  and R 6  are each independently of the others hydrogen, NR 7 R 8 , unsubstituted or substituted C 1 -C 18 alkyl, C 1 -C 18  alkyl wherein the alkylene chain is interrupted with oxygen, unsubstituted or substituted C 1 -C 18 alkenyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl, R 7  and R 8 , each independently of the other, being unsubstituted or substituted C 1 -C 18 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl, 
 optionally a further IR absorber 
 
       and
 exposing the treated material to a laser or IR radiation. 
 
     
     
         2 . The method according to  claim 1  wherein M is Ni, Pd or Pt. 
     
     
         3 . The method according to  claim 1 , 
       wherein
 M is Ni, Pd, Pt, 
 X 1 , X 2  and X 3  are each independently of the others sulfur or oxygen, 
 R 1 , R 2 , R 3 , R 4  are each independently of the others —N(C 1 -C 6 alkyl) 2 , unsubstituted C 1 -C 8 alkyl, —(CH 2 ) n —[O—(CH 2 ) m ] k —OCH 3  with n=2-6, m=2 or 3, k=1-6; vinyl or allyl, —(CH 2 ) q -phenyl with q=1-6. 
 
     
     
         4 . The method according to  claim 1 , wherein the colorless IR absorbers are compounds of formula Ia, Ib, Ic, Id, Ie, If, Ig or Ih. 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         5 . The method according to  claim 1 , wherein the treated material is a security print, an invisible and IR readable bar code, a laser-welded plastic, a cured surface-coating, a dried and cured print, a fixed toner on paper, a laser marked plastic or a heated preform. 
     
     
         6 . The method according to  claim 5 , wherein the treated material is a laser welded plastic. 
     
     
         7 . The method according to  claim 5 , wherein the treated material is a security print or bar codes. 
     
     
         8 . The method according to  claim 1 , wherein the further IR absorbers are polymethines. 
     
     
         9 . Compounds of formulae I and/or II 
       
         
           
           
               
               
           
         
       
       wherein
 M is Ni, Pd, Pt, Au, Ir, Fe, Zn, W, Cu, Mo, In, Mn, Co, Mg, V, Cr or Ti, 
 X 1  is oxygen, 
 X 2  and X 3  are each independently of the other sulfur or oxygen, 
 R 1 , R 2 , R 3 , R 4 , R 5  and R 6  are each independently of the others hydrogen, NR 7 R 8 , unsubstituted or substituted C 1 -C 18 alkyl, C 1 -C 18  alkyl wherein the alkylene chain is interrupted with oxygen, unsubstituted or substituted C 1 -C 18 alkenyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl, R 7  and R 8 , each independently of the other, being unsubstituted or substituted C 1 -C 18 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl. 
 
     
     
         10 . Compounds of formulae I and/or II 
       
         
           
           
               
               
           
         
       
       wherein
 M is Ni, Pd, Pt, Au, Ir, Fe, Zn, W, Cu, Mo, In, Mn, Co, Mg, V, Cr or Ti, 
 X 1 , X 2  and X 3  are each independently of the others sulfur or oxygen, 
 R 1 , R 2 , R 3 , R 4 , R 5  and R 6  are NR 7 R 8 , wherein R 7  and R 8  are each independently of the other unsubstituted or substituted C 1 -C 18 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl. 
 
     
     
         11 . (canceled) 
     
     
         12 . A method of security printing by incorporating the colorless IR absorbers of  claim 9 , into a printing ink and exposing to a laser or IR radiation. 
     
     
         13 . A method of reading bar codes by incorporating the colorless IR absorbers of  claim 9 , into the bar code,
 and exposing to a laser or IR radiation.   
     
     
         14 . A method of laser-welding of plastics, by incorporating the colorless IR absorbers of  claim 9  into the plastic and exposing to a laser or IR radiation. 
     
     
         15 . A method of curing surface-coatings, by treating the coatings with the colorless IR absorbers of  claim 9  and exposing to a laser or IR radiation. 
     
     
         16 . A method of drying and curing a print, by treating the print with the colorless IR absorbers of  claim 9  and exposing to a laser or IR radiation. 
     
     
         17 . A method of fixing of toners on paper or plastic, by treating the toner on paper or plastic with the colorless IR absorbers of  claim 9  and exposing to a laser or IR radiation. 
     
     
         18 . A method of laser marking of plastic by treating the plastic with the colorless IR absorbers of  claim 9  and exposing to a laser. 
     
     
         19 . A method of heating a plastic preform by treating the plastic perform with the colorless IR absorbers of  claim 9  and exposing to IR radiation. 
     
     
         20 . Optical filters for plasma display panels (PDPs) incorporating the compounds of formula I and/or II according to  claim 9 .